About Annapolis and the School

The Sailing School

Founded in 1959 by Jerry Woods, Annapolis Sailing school was the first sailing school for adults in the nation. Prior to our founding, sailing was a hard hobby to get into as an adult. We filled that need, attracting students from all over the country. The school even developed its own vessel, the Rainbow 24, to train our students. When introduced in the 1960’s, these vessels were the first and only to focus on the students’ needs of safety and simplicity. Today, these workhorses still maintain the lead in those areas and are the mainstay of our fleet. Many other schools have popped up to spread the joy of sailing, but Annapolis Sailing School remains committed to teaching sailing in both a fun and relaxing way.

A Sailor’s Town

Annapolis, Maryland, has earned its title as America’s Sailing Capital. With the charm and uniqueness of a colonial seaport, the modern town of Annapolis is a great place to visit by land or water. While you are here, don’t miss our bustling city dock, great seafood restaurants, sailors’ pubs, working boat yards, and boat design firms. Stroll our tree-lined cobblestone streets and discover charming small hotels, quaint shops, bed and breakfasts, and a living museum of colonial and early American history. Unique local institutions like the US Naval Academy and St. Johns College add to the atmosphere of this picturesque town on the Severn River. While visiting us, take a little extra time to discover that there is more to the “Annapolis Way” than just learning to sail.